


First Date

by SRassier



Series: What Might Have Been [2]
Category: The Umbrella Academy (TV)
Genre: First Date, Hitmen, Prequel, Romance, What Else Do I Tag?, hotdogs?
Language: English
Status: Completed
Published: 2020-07-31
Updated: 2020-07-31
Packaged: 2021-03-05 21:06:50
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25621858
Author URL: https://archiveofourown.org/users/SRassier/pseuds/SRassier
Summary: Five and his siblings are tasked with a hit at an art exhibit. Five meets the model of the photos, Delores, and they flirt. They flirt a lot.
Relationships: Dolores/Number Five | The Boy (Umbrella Academy), The Handler/Leonard Peabody
Series: What Might Have Been [2]
Series URL: https://archiveofourown.org/series/1857238
Comments: 6
Kudos: 28





	First Date

**Author's Note:**

> This is a prequel to What Might Have Been. Just a quick little fluff describing how Five and Delores met. You do NOT need to read the original story to enjoy this but I would appreciate it.
> 
> If you choose not to read the original, all you really need to know is that Five, Luther, Hazel, and Cha-Cha are the adopted kids of Mob boss Kate Peabody and her husband, Leonard. The four of them all work as hit-men for their Mom's organization.

Three of the Peabody siblings were milling about in front of their mother’s office door awaiting 10 o’clock. Their mother demanded promptness and did not tolerate anyone being too early either. She insisted that her children show up on time as being late was disrespectful and coming early implied that they were more important that what she was doing prior to their arrival. 

Luther checked his watch. 9:58. He sighed, knowing this meant that his brother Five would be there in one minute. His sister, Cha-Cha, his other brother, Hazel and himself didn’t have the luxury of Five’s power. They had to take care to get places precisely when Mom wanted them to, whereas Five could simply teleport in at the last minute, adding to the long list of reasons he was Mom’s favorite. As far as not being Mom’s favorite, however, Luther was just fine with that.

The clock struck 10 and the large wooden doors opened to reveal their father, Leonard on the other side. Luther lead the way, followed by Cha-Cha, then Hazel. Just as he reached one of the chairs in front of their Mother’s desk, he heard the faint ‘pop’ of Five ripping through space in the hallway and he was the last to enter. The four of them took their seats and waited for their Mother to begin.

Mom was an enigma, Luther thought. On the outside she looked to be the perfect maternal figure. She was beautiful, well groomed, intelligent. She always had a kind word for her children when out in public or when talking to subordinates, but behind closed doors when it was just the family, she could be a tyrant. The best way to live life in this family was to keep your head down and do as you were told, no matter how much you hated it.

“The Calhoun job?” Mom never looked up from her bookwork as she curtly asked the question.  
Luther cleared his throat and answered. “On schedule. Everything will be ready to go by Sunday.”  
“Good.” She scribbled some notes before continuing. “Where are we on the Harper situation?”  
It was Cha-Cha’s turn to speak. “He’s not budging. I’d like permission to take the next step. He’s got a daughter in college. We could snatch her up, he’d cave in a matter of hours.”  
Mom looked up at Cha-Cha and glanced at Hazel for his agreement. A simple nod gave it and she said, “Do it.” She put down her pen and looked across the four faces sitting in front of her and smiled. “I am so proud of all of you.”  
“Here we go,” Five muttered under his breath, gaining a stern look from her but nothing more.  
“I know it’s been a while since you all got to do something really fun, so I’ve got a special job for tomorrow night.”

Five and Cha-Cha perked up as Luther and Hazel slumped in their chairs. Their Mom’s idea of ‘fun’ was either ultra-violent, which catered to their sister’s area of expertise, or something Hazel called ‘James Bond wanna be spy shit’ which was right up Five’s alley. “I have two tickets to the Gorman Gallery’s new art exhibit.” The four of them made no noise, but she got four looks of confusion as she went on. “All of the art is from this photographer and his ‘muse’…some model named Delores.”  
“Never heard of her.” Cha-Cha huffed out.  
“That’s because you don’t waste your time with such frivolities my dear.” Mom smiled her sickly-sweet smile at her only daughter and continued. “The photographer is actually the head of the Tataglia crime family out of Chicago. His ‘art’ is his hobby and this exhibit is supposedly something he’s been working on for quite some time. It’s his baby, Delores is his inspiration, blah, blah, blah…Point is. He will be in town, he will be vulnerable, and now is our chance to take him out and move our way into Chicago.”

Five had abandoned his air of not caring and had turned on his mission brain. “Why only two tickets? Who’s going in?”  
“You are all going in. Cha Cha and Hazel will be going in as staff.” Hazel rolled his eyes, awarding him a swat on the back of the head from Dad. “Luther and you will be attending the party.”  
“Who’s taking point?” He always asked, even though the answer was always the same. He knew that she trusted him more than Luther to keep a mission on track. Luther was strong, and smart, but his heart wasn’t in it.  
Mom could barely hide her amusement at Five’s shocked face when she answered, “Luther.”

“Luther?” Five sat up and saw his brother do the same out of the corner of his eye.  
“Yes. Luther is to be the sole trigger man on this job. I need to you to do something else.”  
“What the hell am I supposed to do?”  
“Tataglia and Delores are inseparable. She is rarely seen without his arm around her. I’d like to keep the collateral damage at a minimum. Her disappearing or winding up dead would bring a lot of heat on our organization once Tataglia’s body is found, so you are to be a distraction while Luther takes care of our man.”  
“A distraction?”  
Cha-Cha spoke up, “So, Hazel and I have to act as glorified lookouts while serving champagne to upper crust morons while Luther gets to have all the fun and Five basically just has to go on a date?”  
Mom glared at her only daughter. “If I thought you or Hazel could successfully seduce a gorgeous model, Five would be serving champagne to the ‘upper crust morons.’ As it stands, however, I have chosen the most well-bred of the lot of you.”

Luther opened his mouth to add to the conversation but was cut off when Mom looked back down to her book and barked, “dismissed.”  
Dad walked to open the door for the group, and they knew the conversation was over. They trudged out single file and Dad handed Five the two tickets as he was the last one out. “So,” Five beamed brightly at his siblings, “lunch?”

~~~~~~

The next evening found Luther and Five mingling with high society and pretending to care about stocks, fine champagne, or the art that was in front of them. As they looked at the photographs of Delores, a woman decked out from head to toe in vintage fashions and hairstyles, looking like a pin-up girl from the 1940s, Five couldn’t help but comment to a very bored Luther, “She is quite stunning…my job is looking better and better by the minute.”  
“Well, I’m glad you’re so happy about it.”  
Five looked over at his brother and put a hand on his shoulder. “Sorry big guy, I know you hate these types of missions.”  
“It’s not a ‘mission.’” Luther shrugged Five’s hand off his shoulder. “Stop acting like we’re spies or some shit…we are mob hitmen, plain and simple.”  
“Jesus Luther,” Five looked around to see if anyone was in earshot. “Declare it to the room why don’t you?”  
“Sorry.” Luther tilted his head in the direction of the balcony and Five looked. There stood their target and at present time, he seemed to be breaking away from the model of the hour, kissing her hand and offering apologies as another man in a suit whisked him away. “Let’s get this over with.”

Luther nodded to Hazel and the two of them followed Tataglia out of the room as Five swooped by Cha-Cha, grabbing two glasses off her tray and winking at his sister’s perpetual scowl before walking out onto the balcony. “Hi.”  
Delores turned around to face him and his words caught in his throat. “Uh…for you.” She reached out and took the offered glass nodding a thank you before taking a sip of the bubbly liquid. “You’re her right?” Five motioned to the art inside.  
Delores chuckled, “yeah, I’m her.”  
“Well, I’m sorry to tell you this but…” Five looked at her with a pitying look. “Those pictures are absolute garbage.”

Delores’ eyes went wide, and her brows scrunched into a scowl. “Excuse me?”  
“I’m just being honest.”  
“There’s being honest, and there’s being an absolute prick. Didn’t your mother teach you to be respectful?”  
Five took a sip of his champagne and smiled back at her. “She taught me not to lie and I didn’t. Those pictures. Are. Garbage.” 

Delores put her glass down on a table and turned to leave the balcony but Five gently grabbed her arm and turned her around to face him again. “You didn’t let me finish.” She crossed her arms in front of her chest and gave him an incredulous look. “They are garbage because while you do look pretty in them, seeing you in real life makes you realize that a photograph will never be enough to portray how gorgeous you really are.”

She slowly lowered her arms and raised an eyebrow at him. “Alright, that was a pretty good line.”  
“It wasn’t a line. Remember, my Mother taught be to be honest.” He took another sip of his champagne and winked.  
Delores picked up her glass and sauntered back to the balcony to look over at the city. Five followed. “You know what my Mom always told me?”  
“What’s that?”  
She gave him a side glance, “She said that there is nothing sexier than a guy who can have an entire conversation with you and never check out your body once.”  
She turned fully toward him and he took a step in her direction, causing their bodies to be mere inches from each other. He leaned in close and without breaking eye contact he said, “Oh, I looked. I’m just exceptionally good at being discrete.”

“What’s your name?”  
“Five.”  
“That’s an interesting name, Five. Do you have an interesting profession to go with it?”  
“I do.” Five purposely lifted his glass for another drink.  
“Well…?”  
He looked at her with a raised eyebrow. “I don’t know if you’ve earned that yet.  
“Ooh, I like this game. What exactly do I have to do to earn some more information about you?”  
Five looked up and to the left as he let out a faint, ‘hmm…’ His eyes finally fell back to hers and she couldn’t help but notice that he had gotten even closer to her, if that was possible. “Let me buy you a hot dog.”

Before Delores could react to the bizarre request, Luther poked his head out to the balcony and called out, “Five.”  
Five never broke eye contact with Delores as he mumbled a halfhearted, “Huh?”  
“It’s done, let’s go.”  
“Yeah, I’m gonna stick around for a while.”  
“Five…”  
Five finally turned to his brother and shot him his best ‘you are not welcome here’ look. “Luther…”  
Luther straightened his back and huffed. “Fine, but don’t do anything stupid. 10 am tomorrow.” With his warning hopefully absorbed by his twin, Luther turned and left.

“Two questions.” Delores reached up and started absentmindedly playing with Five’s tie.  
He looked down at her hands and back at her. “I am an open book.”  
“First, what’s done?”  
Five’s face suddenly changed from the jovial almost playful look he had had since he met her on the balcony into something more serious, more severe. She kept his gaze as he seemed to be struggling with the words that he wanted to speak. Finally he settled on, “What’s the second question?”  
“Why a hot dog?”  
Five grinned. “Because I’ll bet no one has ever offered to buy you some cheap-ass, greasy, street food before.”  
“You’re right. Usually guys try to impress me.”  
Five put his empty glass down and took her hands away from his tie, holding them in place at his chest. “I’m plenty impressive. Being of such high quality, I can get away with offering junk food for a first date.”

Delores squeezed his hands in hers and spoke more daringly than she had in a long time. “I let you take me away from this party and get a hot dog…you tell me what that guy meant by ‘it’s done.’”  
Five considered her proposal. “Done.” He turned and offered her an arm and she took it. The two strolled past hordes of onlookers wondering where the hell Delores was going with this mystery man.

~~~~~~

Half an hour later, Five and Delores sat on a park bench about a half a block from the hot dog stand that Five swore would ‘change her life.’ The life changing sausage sat uneaten, however next to her as she tried to take in all that he just told her. “Like, the mob, the mob?”  
“Yup.” Five ate the last bite of his hotdog and gave her half a smile. He was impressed at how well she was taking it all. It wasn’t every day you meet a guy, agree to a date, and then find out that the whole time you were flirting with him, his brother was killing your photographer because their mother, a mob boss had ordered a hit on him.  
“Why?”  
Five wiped his mouth with a napkin. “She wants his Chicago territory.”  
“No, I mean…why did you tell me?”  
Five figured that honesty was working ok for him so far, might as well keep it going. “Because when I first saw you, I knew I was going to try to sleep with you and I refuse to start a relationship with lies.”  
“A relationship?”  
Five put his hand on his chest in mock offence. “You don’t think I’m just a ‘one-and-done’ kind of guy, do you?”

Delores picked up the hotdog and took a bite, noticing that Five was giving her space to take in all that she experienced this evening. She chewed carefully and once she swallowed the first bite she smiled. “You’re right, this is a really good hot dog.”  
“I told you, I’m not going to lie to you.”  
She took another bite and made a note of how he watched her mouth as she swallowed. Licking her lips slowly, she stood from the bench and offered him her hand. He took it and stood up and as he did, she leaned in and whispered slyly, “let’s see if you were telling the truth about not being a ‘one-and-done’ kind of guy.”

~~~~~~ 

Delores was in that dreamy haze halfway between sleep and awake when suddenly her phone buzzed loudly, startling her into a sitting position. Five mumbled something incoherent next to her as she pressed the accept call button. “Hello?”  
“Delores? It’s Marcy.”  
“Marcy?” Delores looked at her bedside clock. “It’s 3 am.”  
“I know, I’m sorry to bother you so late but I wanted to tell you before you saw it on the news.”  
Delores was now completely awake and vaguely aware of the man stirring into a sitting position next to her. “What are you talking about?”  
“It’s Anthony…” Delores knew what was coming next. “He’s dead.”  
“What?” Delores was a model, not an actress, but in that moment, she thought she was doing a pretty good job.  
“Yeah, the staff at the party found him while they were cleaning up. Someone shot him and threw him in the dumpster out back…like they wanted him to be found.”

Any doubt Delores had about Five’s story slowly faded away as Marcy continued, talking about how her cop friend said it looks like a mob hit but they don’t have much to go on. “Anyway, this is just a heads up that the cops are going to want you to come in and give a statement.”  
“Ok, thanks Marcy.” Delores ended the call and slowly placed her cell on the bedside table.  
“Everything ok?” Five reached out to rub the side of her arm.  
“My photographer Anthony.” She turned to look at him. “He was killed last night.”  
“Really?” He laid back down and put his arms behind his head on the pillow. “That’s a tragedy.”  
“Not really.” Five looked at Delores with some confusion. “He was an absolute prick. He just took really good pictures.”  
“So you’re telling me that you don’t mind being with guys with questionable morals as long as they have an eye for beauty?”

Delores shifted herself so she was laying half on top of him. She leaned in and her mouth was nearly on his when they were interrupted by The Imperial March from Star Wars. “Damn it!” Five rolled out from under her and grabbed for his pants on the floor. He fished the phone out of his pocket and answered it. “Hi Mom…Yes…No I’m not at home…I’m uh…” He looked over his shoulder at Delores. “I’m with Delores…yes the model from the party…no she has no idea…she thinks I’m a stockbroker.” Delores raised an eyebrow and smirked at his side of the conversation. “Mom!” He pursed his lips and Delores could hear a faint voice on the other end of the line doing what sounded like scolding. Five turned away and cover the speaker as best he could and whispered into the phone, “Yes I used protection…yes I will be at the meeting tomorrow…good night Mom…GOOD NIGHT MOM!” 

He pressed the button and tossed his cell onto the crumpled pile of his clothes before dropping his head into his hands in embarrassment. Delores propped herself up on one elbow. “Why is it ok to lie to your mom, but not your girlfriend?”  
Five slowly raised his head, turned around and plopped down on the bed in a position mirroring her. “My girlfriend?”  
Delores leaned forward and placed a kiss on his lips before whispering, “you didn’t think I was just a ‘one-and-done’ kind of gal, did you?”

**Author's Note:**

> As always, comments are the life blood of fan fiction writers, but even if you do not comment...thanks for reading!!!


End file.
